Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory

Yeliz Utku, Abhinav Rohatgi, Barney Yoo, Kent Kirshenbaum, Ronald N. Zuckermann, Nicola L. Pohl

Research output: Contribution to journalArticlepeer-review

Abstract

Peptidomimetic compounds are increasingly important in drug-discovery applications. We introduce the synthesis of an N-substituted glycine oligomer, a bioactive "peptoid" trimer. The six-step protocol is conducted on solid-phase resin, enabling the synthesis to be performed by undergraduate organic chemistry students. This synthesis lab was successfully completed within one 4-h session by second-year students. The procedures are relatively inexpensive and versatile, enabling modifications to generate a variety of oligomer sequences from commercially available reagents including bromoacetic acid and a diverse set of primary amines.

Original languageEnglish (US)
Pages (from-to)637-639
Number of pages3
JournalJournal of Chemical Education
Volume87
Issue number6
DOIs
StatePublished - 2010

Keywords

  • Combinatorial chemistry
  • Drugs/pharmaceuticals
  • HPLC
  • Hands-on learning/manipulatives
  • Laboratory instruction
  • Mass spectrometry
  • Medicinal chemistry
  • Nucleophilic substitution
  • Organic chemistry
  • Proteins/peptides
  • Second-year undergraduate
  • Synthesis
  • Thin layer chromatography

ASJC Scopus subject areas

  • Chemistry(all)
  • Education

Fingerprint Dive into the research topics of 'Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory'. Together they form a unique fingerprint.

Cite this